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As Rory and Lorelai enter the diner to get breakfast, they meet with a fully overstressed Luke, trying to organize the funeral of his dead uncle while managing breakfast rush at the diner.
Rory notices Jess isn't even there to help.
"Hey Luke, where is Jess?", she asks.
"I don't know."
"School?", she tries.
Luke laughs: "Please, probably upstairs."
Rory can't believe her ears. "Really? Excuse me."
She just hates seeing how different he acts with others. With her, he's nothing but sweet, smart and funny. With everyone else, he keeps showing this "I don't care about anything or anyone" personality.
She storms upstairs, ready to yell at him for being so lazy and to force him to come downstairs to give a hand.
She knocks on the apartment door. She knocks again louder. "Jess, open up! I know you're in there".
As nobody answers, she gets even more worked up for how unwilling to help Jess is, opens the door and storms inside the apartment.
"Luke needs you downstairs! He's on the phone, the place is packed and he needs -"
She stops mid-sentence as she finds Jess sitting in bed, his right hand deep in his pants while his left hand pulls the headphones out of his ears. Quickly, he pulls his right hand out of his pants. "Rory, JEEZ!"
She freezes a second with her eyes wide open. She can't believe what she's just seen. How stupid she has been to just storm in like that!
When she remembers how to breathe, she turns around and says to the wall in front of her: "the diner is packed and Luke needs you and oh my god I'm so sorry I should have knocked louder and -"
Jess sighs and tries to calm her down: "Don't worry, let's just forget about it. Obviously I wasn't prepared to see you walk in like that, but it's not like you've caught me doing anything shameful. Everybody masturbates, it's nothing to be ashamed of."
As Rory stays frozen, he feels like adding more explanation: "Sharing a room with Luke, I hardly ever have any privacy so this morning felt like a good opportunity to get some alone time. But sure, I'll come downstairs in a minute and help Luke out."
Rory finally says "Fine." And disappears out the door.
When Jess enters the diner, Lorelai is paying at the cash register. He goes straight to Rory's table, hoping to check in if everything's okay. He barely has time to say "hey, can we talk?", she gets up, says "sorry, I'm late for school!" And storms out the door. Jess picks up the book she left on the table and gives it to Lorelai: "here, Rory just left her book on the table". "Oh, thanks, Jess!" she says, before joining Rory outside the diner.
Later that day, when Jess comes back from school, Lorelai is sitting at the counter, talking to Luke. Jess doesn't usually talk much to Lorelai, but he is getting kind of worried that Rory might be avoiding him. "Lorelai, I don't think I've ever seen you alone here. Did Rory get lost?", he tries to sound casual. "Oh yeah, she had some last-minute homework she needs to work on." She turns to Luke "She's actually ditching me for the town meeting, can you believe that? I never attend a town meeting alone, I need someone to share sarcastic comments with, otherwise it's not a real town meeting. Will you come with me?"
A few hours later, as Luke leaves to the town meeting, Jess is pacing in the apartment with the phone in his hand. He knows Rory is alone at home, so now could be a perfect moment to finally talk to her. But he also does want to give her some time and space if she needs to process what happened. He realizes this morning might have been more of a shock for her than for him and he really wants to clear the air with Rory and check that she's okay and that this won't change anything between them. Also, he hasn't apologized yet and he does want to say he's sorry for having made her uncomfortable.
He dials her number.
"Hey Rory, it's me, Jess.
Please don't hang up!
I just wanna say I'm sorry that you got to see me in that position this morning. I understand it's made you uncomfortable and I just hope we can forget about it and just go back to normal..."
"..."
"Rory? Do you want to hang up or say something?"
"It's not that.", she finally answers.
"... Sorry?", Jess asks, surprised.
"I'm sorry I've been avoiding you, I've just been upset about something you said."
"Oh, ok." Jess searches his memory but can't remember saying anything upsetting. "What did I say?"
He hears Rory hesitate, then answer: "Well, you know, you said it's nothing to be ashamed of and everybody does it."
"Yes, and..?"
"Well... I don't. I mean, I haven't."
Jess suddenly understands: "Oh, you..? You've never..?"
"..."
He feels like an idiot for upsetting her even more, when he was trying not to make a big deal out of the situation: "Oh Rory I'm so sorry! I didn't mean everyone should do it, I just meant that it's pretty common. Of course, people should only do it if they want to, i'm sure a lot of people don't want to and it's totally okay."
She interrupts him: "No, it's not that I don't want to. I just... I wouldn't even know how to do it."
"Oh, okay. Well that's one of the points of doing it: it's getting to know yourself. To try and see what feels good, what doesn't work and what works particularly well for you. I had a conversation about it with some friends who are a bit older, and they said they wish they had gotten to know themselves first, before getting intimate with a partner and hoping that their partner would magically know what to do. But a partner can't know what feels good for you, that's something only you can tell. So, if you feel like it, you can try and discover yourself."
"..."
Jess fears he might have upset her again! "But again, it's no obligation and just like sex with a partner, it's something we should only do when we really want to and when we feel safe enough to relax and to have fun doing it."
He is relieved to hear that she doesn't sound upset anymore: "Mmh that does sound nice. But honestly, this is so embarrassing, but like I can't even imagine how to start. Like, really, what do I even do?"
"..."
"Jess?"
"Oh, are you asking me? I thought that was a rhetorical question!", Jess panicks.
"No, I really don't know... I don't think I feel comfortable enough to bring up the subject with my mom or any of my friends, so..."
Jess isn't sure he understands what she's asking him. "Hum... Rory?"
"Yeah?"
"I guess, hum... I mean if you wanted to, I could tell you what I know about it, or at least give you an idea where to start. I mean, obviously not everything works for everyone and you'll have to figure it out on your own, but-"
"Yes!" she interrupts him.
"Wh-what?" Jess asks, slightly overwhelmed.
Rory repeats, more clearly: "Jess, yes, please tell me what to do."
Now, Jess has no doubt what she's asking him. He's needs a moment to process what is happening.
"Oh, ok! Yes, sure.
Hum... Ok!
Before we start, please promise me that if this gets uncomfortable for you or if you want to stop at any time - really any time - please promise to interrupt me or just hang up, ok?"
"Okay."
"You promise?"
"Yeah, I promise."
Jess starts: "Ok, so, I guess it's best if you lie down somewhere comfortable, maybe in your bed? Like, you get under the blanket, lie on your back and get comfortable. If you feel tensed or nervous, you can take a few deep breaths."
Rory breathes loudly in and out.
"Oh, are you doing it right now??", Jess asked, shocked.
"Uh, yeah. Shouldn't I?" she answers, sounding confused.
"Oh, well, I... I thought I was just explaining the theory so you could do it later. But I mean, if you feel like doing it while I explain-"
Rory interrupts him: "Oh, sorry, I thought it was implied! No, no, of course I can do it later. Sorry!"
"No, don't be sorry.", Jess reassures her, his voice now calmer. "It's actually okay with me if you want to do it now, I mean if you're comfortable doing it..."
"Sure?", she checks.
Jess answers, short of breath: "Yeah."
"Well, yes, I'd like that."
Jess gathers his courage to resume:" Ok, so-"
Rory helps him: "Deep breaths, yes."
Jess hears Rory breathing loudly in and out again, and takes the opportunity to take a few deep breaths himself, until he feel his heartbeat going back to normal.
Then he takes over where he left off, his voice now calm and soothing:
"Close your eyes. With both hands, start stroking your face very lightly. Whichever part you feel like touching: your eyebrows, your temples, your cheeks, your chin, your lips... Just enjoy the touch of your soft skin with your fingertips. You can take your time." He pauses.
"Whenever you're ready, let your fingers slide down to the back of your neck, to your collar bones."
"Then you can pull the blanket down a bit and use your hands to brush your full body top, from your bellybutton up to your breasts, then down again and up again... You can feel what body parts your hands want to go back to again." He pauses.
"Does that feel okay?"
"Hm, hm."
"Should I keep going?"
"Yes, please." Rory says timidly.
A light smile appears on Jess' lips. He can relax a little, knowing that he's doing okay. He focuses again on the thought of Rory's hands on her body. He takes a deep breath.
"If you hands happen to brush over your nipples, you might feel them hardening."
Jess hesitates for a second before talking further: "Now, you might feel like pulling up your shirt and repeating the same gestures that felt good, with direct contact to your skin."
He pauses for a bit.
"Rory?"
Rory answers with a distracted voice as if he'd interrupted her: "Yes?"
"Is that still okay?", he checks.
"Mh mh, yes."
"Okay. So I'll go on, yeah?"
"Yes, please."
"So..." Jess takes a deep breath, then dares to take one more step:
"One of your hands can stay in this area while the other goes a little further down.
Oh, but before that, it's best if you bend your legs to place your feet flat behind your butt on the bed, so your knees are above your hips. You know what I mean?"
"Yes."
"Then pull your knees apart to open your legs, as far apart as you're comfortable. It's fine if they're only hip-wide apart. In case you feel like opening them completely and letting your knees fall on each side on the mattress, you might feel more comfy placing a cushion under each knee."
Jess hears Rory fumbling with cushions and can't help but imagine her lying on her bed, with her t-shirt pulled up and her knees wide open. His thoughts are interrupted by Rory's voice:
"So, one hand goes down to where?"
He comes to his senses: "Yes! So... One hand can stay where it is and kind of automatically wander over the top of your body, without really thinking about it. And the other hand can explore a little further down. Your fingers might want to slide down your hip to the outside of your thigh, and brush very lightly to the inside of your thigh..." Jess swallows his breath.
"Then, whenever you feel ready, your hand might want to brush over your pubis, then down to your vulva. Very lightly at first. Unless you're wearing jeans or another thick fabric, in this case you might need to apply a bit more pressure to be able to feel your touch through the fabric. If you're wearing a light fabric -"
"Yes"
"Sorry?", he asks, startled.
"Yes, I'm wearing pyjama bottoms, so rather a light fabric."
Hearing Rory share this detail with him makes Jess' heart miss a beat. She is feeling comfortable doing this with him.
He goes on: "So, you could start stroking that whole area with light, slow touches. When -if! You feel like it, you can stroke circles, targeting where your clitoris is. I don't know if you know where... Well, it's located at the top of your vulva, where your inner lips meet. Do you know what I mean?"
"Yeah, I think so."
"Okay, you don't need to feel precisely where it is now, you can just stroke large circles around it with your fingers. You can go from slow, big circles to faster, smaller circles. Then you slow down again and so on."
Jess pauses.
"You can also take breaks from the circles and let your fingers explore this whole area, then go back to the circles."
Jess pauses again to think.
"This might feel enough for your right now and you might want to stop there. You can keep exploring over your pyajama bottoms.-"
"Or..?" she asks.
"Or, we can take a step further - I mean YOU can take a step further. You might feel like exploring further without any fabric between your fingers and your body."
"Yes."
"Yes?"
"Yes."
Jess can't believe the words he hears coming out of his mouth: "Okay, so take off your pyjama bottoms. If you're wearing panties-"
"Yes"
"Keep them on. Enjoy this last piece of fabric and play with the circles again, targeting your clitoris. Slow, big circles getting smaller and faster, then slow and big again. Your fingers might also wanna play with the rubber bands of your panties, feeling this last barrier between your fingers and your vulva: slide your fingers slightly under the elastic and then pull them out again...
Until you're ready to let your fingers slide completely into your panties. Let them feel the touch under your fingertips as they explore deeper inside your panties...
What you can do is feel down to the entry of your vagina, and you might feel some wetness.-"
"Oh!", Rory gasps.
Jess feels suddenly very hot as he realizes that Rory just gasped while feeling how wet she is. He swallows his breath and asks in a whisper: "Are you?"
"What?"
"Are you- um, are you wet?"
"Yes. Very..."
Jess' brain freezes for one second.
Then the words leave his mouth before he properly thinks about what he's asking: "Rory, do you mind if I uh.. touch myself? Would that be okay?"
Rory sounds breathless as she answers: "Yes."
"Sure?"
"Yes, sure. Are you, um..?" She asks hesitantly.
"Hard?" Jess dives a hand inside his pants. "Yes! But I don't want to let it distract us from my instructions, so I'll stop if I feel like I'm losing focus, okay?"
"Mh, mh." Rory answers, then encourages Jess to resume where they left off: "So, my fingertips are feeling the wetness and then?"
Jess prevents himself from moaning with arousal as he hears Rory say this. He focuses again.
"So, you kind of "dip" two or three fingertips in and slide the wetness up to your clitoris. From there, you start the circles again : slow... Big circles... Then faster circles, getting smaller and smaller and faster... Then bigger and slower again... And you add some wetness anytime you feel like it."
Jess pauses to let Rory experiment with what he's just told her. He uses this pause to start moving his hand, which has been holding his penis firmly since Rory said it was okay for him to touch himself. As his hand gets active, he pictures what Rory's hand is doing and how these new sensations might be feeling for her.
Again, he can't believe the words he hears come out of his mouth: "You can take off your panties if you want to. You can also try and change the direction of the circles, see how it feels." His voice is practically whispering by now. While he says this, his own hand is also playing with the pressure and speed of his grip.
As he feels like moaning, he whispers to Rory: "If what you're doing feels good, you might feel like making some sounds, lke moaning. If this is the case, feel free to let it out, express what you're feeling."
He lets a moan escape as he hears a low moan from Rory's side.
This feels so intimate that he adds: "You know, you can mute your phone if that makes you feel more comfortable? You should be able to fully experience what you're feeling and not feel limited by knowing someone can hear you."
"It's fine.", she answers without hesitation.
"Are you sure-"
"I want to hear you too."
Jess hears himself moan with pleasure and relief. It feels so good to hear that Rory's willing to share this intimacy with him, that he's allowed to feel as turned on as he's feeling right now.
If Rory is as aroused as he is, he imagines she is also ready for things to get more intense.
He checks in a whisper: "Are you ready to keep going?"
She answers yes in a long whispered moan.
"You're gonna want your second hand to slide down to your vulva, too. While the first hand keeps doing circles, to the rhythm and pattern that feel best for you, with your second hand you're gonna slide one finger into your vulva. Not just the tip like we've done until now. Deeper in. Just slide it inside, then out again. Then inside, then out again."
As he says this and hears Rory moan with surprise, Jess can't help but stroke himself faster.
"Now I want you to stop thinking: you just let your hands do what they're doing to the rhythm that feels good to you, and you let yourself go. Moaning definitely helps letting go-"
Rory says in a moan: "I want to hear you too."
"What?"
She repeats, clearer: "I want to hear you let go with me."
Jess doesn't answer and just allows himself to moan as he imagines Rory's finger sliding inside and out of her, as she keeps rubbing her clitoris and allows herself to feel good... Really good... So good... Mhhh... Mmmh.. he hears her moan, longer and louder, as he allows himself to do the same... Mmmh... MMMMMHHHH... They moan more and more intensely together, until he is suddenly pushed over the edge as he hears her moans getting high-pitched and uncontrolled.
She lets out a few more moans, sounding like a mixture of relief, content and exhaustion. He remains silent, lets his breath getting slower and gives her a little time.
He whispers: "Rory? Are you still there?"
"Mh, mh.", she sounds like she's smiling.
"Hum, so..." He smiles softly: "We're not quite done yet, now comes the after care. It's the moment when we express how we feel after the intimate moment we've just shared." He pause. "So... how do you feel?"
"..."
He interprets her silence as an hesitation. "Rory? Should I start?"
"Mh, mh.", she confirms.
"I... I feel so lucky that I got to share this moment with you. It felt so intimate, I felt so close to you, even though we're not even in the same room. I just really hope it was okay that I interfered like this, actually it was supposed to be all about you discovering your pleasure and I'm a little worried that I should better have left my pleasure out of it...-"
She interrupts him: "Jess, it was so good. Not only physically, but just sharing this with you was amazing. I just wish you were here and could hold me in your arms."
Jess feels a huge smile growing on his face as well as a little tear forming in the corner of his eye.
"Yeah, it would feel good to hold you in my arms. I mean, I'm literally just a couple of streets away from you." He hesitates. "Could I come over for a hug?"
"You would do that? Yes!"
"I'll be there in 10 minutes. Make sure to go to the toilet - it's something you should do every time you have sex, to avoid any urinary infection. I can't wait to hold you!"
He hears her smile: "Ok, you can hang up, now. I'll see you soon!"